Trimethylamine → HCID 131718968, compound

HRID 1654534Notes

Reaction equation

HRID 1654534 reaction equation
[CH2:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[CH2:3][CH:2]1[CH2:10][C:11]([CH:13]1[S:17][CH2:16][NH:15][C@@H:14]1[C:18]([N:20]1[CH2:26][CH2:25][CH2:24][C@H:21]1[CH2:22][OH:23])=[O:19])=[O:12].CN(C)C>CS(C)=O>[CH2:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[CH2:3][CH:2]1[CH2:10][C:11]([CH:13]1[S:17][CH2:16][NH:15][C@@H:14]1[C:18]([N:20]1[CH2:26][CH2:25][CH2:24][C@H:21]1[CH:22]=[O:23])=[O:19])=[O:12]

Participants

4

Reactant 2

HCID 1146TrimethylamineHCID 131718966HCID 131718966, compound

Product 1

HCID 131718968HCID 131718968, compoundYield 18.2%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent2×

Procedure

1-[3-(Indan-2-ylacetyl)-L-thioprolyl]-L-prolinol (590 mg) and trimethylamine (1.32 ml) were dissolved in 1.50 ml of dimethyl sulfoxide, followed by addition of 1.55 g of sulfur trioxide-pyridine complex dissolved in 2.25 ml of dimethyl sulfoxide at room temperature under agitation, which was then agitated for 15 minutes. The reaction solution was placed in ice-cold water, followed by extraction with chloroform. The organic phase was washed sequentially in 5% HCl, saturated aqueous sodium bicarbonate solution, saturated aqueous sodium chloride solution, followed by drying over anhydrous magnesium sulfate. After distilling off the solvent under reduced pressure, the residue was purified by column chromatography, to obtain 107 mg of 1-[3-(indan-2-yl acetyl)-L-thioprolyl]-L-prolinal. Yield; 18%.

Workup

  1. additionfollowed by addition of 1.55 g of sulfur trioxide-pyridine complex
  2. extractionfollowed by extraction with chloroform
  3. washThe organic phase was washed sequentially in 5% HCl
  4. dry with materialby drying over anhydrous magnesium sulfate
  5. distillationAfter distilling off the solvent under reduced pressure
  6. customthe residue was purified by column chromatography

Sources & evidence

ORD record
ord-51bb5cb9d1954479a78058473d67f00b
Source dataset
uspto-grants-1995_04
Patent number
US05407950

Reaction notes

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